Copper(I)-catalyzed cycloaddition of bismuth(III) acetylides with organic azides: Synthesis of stable triazole anion equivalents

Angewandte Chemie - International Edition

Volumn 52, Issue 49, 2013, Pages 13037-13041

  Worrell, Brady T ^a   Ellery, Shelby P ^a   Fokin, Valery V ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

bismuth; click chemistry; copper; cycloaddition; heterocycles

Indexed keywords

1 ,2 ,3-TRIAZOLES; CLICK CHEMISTRY; COPPER CATALYST; FUNCTIONALIZED; HETEROCYCLES; MILD REACTION CONDITIONS; ORGANIC AZIDES; REACTIVE INTERMEDIATE;

BISMUTH; COPPER; CYCLOADDITION; FUNCTIONAL GROUPS;

NITROGEN COMPOUNDS;

AZIDE; BISMUTH; COPPER; MONOVALENT CATION; ORGANOMETALLIC COMPOUND; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CLICK CHEMISTRY; CYCLOADDITION; HETEROCYCLES; SYNTHESIS;

BISMUTH; CLICK CHEMISTRY; COPPER; CYCLOADDITION; HETEROCYCLES;

AZIDES; BISMUTH; CATALYSIS; CATIONS, MONOVALENT; COPPER; CYCLOADDITION REACTION; ORGANOMETALLIC COMPOUNDS; TRIAZOLES;

EID: 84888602200     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201306192     Document Type: Article

References (43)

1. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708
2. Angew. Chem. Int. Ed. 2002, 41, 2596
3. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057.
4. P. Wu, V. V. Fokin, Aldrichimica Acta 2007, 40, 7-17
5. M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952.
6. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128
7. M. Whiting, J. C. Tripp, Y.-C. Lin, W. Lindstrom, A. J. Olson, J. H. Elder, K. B. Sharpless, V. V. Fokin, J. Med. Chem. 2006, 49, 7697
8. B. L. Wilkinson, L. F. Bornaghi, T. A. Houston, S.-A. Poulsen, Drug Design Research Perspectives, Vol. 57 (Ed.:, S. P. Kaplan,), Nova, Hauppauge, 2007.
9. A. J. Link, D. A. Tirrell, J. Am. Chem. Soc. 2003, 125, 11164
10. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192
11. J.-F. Lutz, Z. Zarafshani, Adv. Drug Delivery Rev. 2008, 60, 958.
12. C. J. Hawker, V. V. Fokin, M. G. Finn, K. B. Sharpless, Aust. J. Chem. 2007, 60, 381.
13. R. A. Evans, Aust. J. Chem. 2007, 60, 384
14. J. A. Johnson, J. T. Koberstein, M. G. Finn, N. J. Turro, Macromol. Rapid Commun. 2008, 29, 1052.
15. J. E. Hein, J. C. Tripp, L. B. Krasnova, K. B. Sharpless, V. V. Fokin, Angew. Chem. 2009, 121, 8162
16. Angew. Chem. Int. Ed. 2009, 48, 8018
17. C. Spiteri, J. E. Moses, Angew. Chem. 2010, 122, 33
18. Angew. Chem. Int. Ed. 2010, 49, 31.
19. Intermolecular couplings J. Deng, Y.-M. Wu, Q.-Y. Chen, Synlett 2005, 2730; Intramolecular couplings
20. J. Panteleev, K. Geyer, A. Aguilar-Aguilar, L. Wang, M. Lautens, Org. Lett. 2010, 12, 5092
21. J. M. Schulman, A. A. Friedman, J. Panteleev, M. Lautens, Chem. Commun. 2012, 48, 55.
22. B. H. M. Kuijpers, G. C. T. Dijkmans, S. Groothuys, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Synlett 2005, 3059
23. D. V. Partyka, L. Gao, T. S. Teets, J. B. Updegraff, N. Deligonul, T. G. Gray, Organometallics 2009, 28, 6171
24. Y. Zhou, T. Lecourt, L. Micouin, Angew. Chem. 2010, 122, 2661
25. Angew. Chem. Int. Ed. 2010, 49, 2607.
26. For selected reviews on the subject, see L. D. Freedman, G. O. Doak, Chem. Rev. 1982, 82, 15
27. J.-P. Finet, Chem. Rev. 1989, 89, 1487
28. H. Suzuki, T. Ikegami, Y. Matano, Synthesis 1997, 249
29. G. I. Elliott, J. P. Konopelski, Tetrahedron 2001, 57, 5683
30. Organobismuth Chemistry (Eds.:, H. Suzuki, Y. Matano,), Elsevier, Amsterdam, 2001
31. J. Luan, L. Zhang, Z. Hu, Molecules 2011, 16, 4191.
32. Untethered bismuth(III) acetylide complexes H. Hartmann, G. Habenicht, W. Reiss, Z. Anorg. Allg. Chem. 1962, 317, 54
33. K. Rudolph, M. Wieber, Z. Naturforsch. B 1991, 46, 1319
34. Y. Matano, M. Kinoshita, H. Suzuki, Bull. Chem. Soc. Jpn. 1992, 65, 3504; Tethered bismuth(III) acetylide complexes
35. H. Suzuki, T. Murafuji, N. Azuma, J. Chem. Soc. Perkin Trans. 1 1992, 1593
36. S. Shimada, O. Yamazaki, T. Tanaka, Y. Suzuki, M. Tanaka, J. Organomet. Chem. 2004, 689, 3012.
37. K. Ohkata, S. Takemoto, M. Ohnishi, K.-y. Akiba, Tetrahedron Lett. 1989, 30, 4841.
38. T. Ogawa, T. Ikegami, T. Hikasa, N. Ono, H. Suzuki, J. Chem. Soc. Perkin Trans. 1 1994, 3479.
39. S. Oae, Y. Uchida, Acc. Chem. Res. 1991, 24, 202.
40. 0 catalyst, diaryl ketones, rather than 1,2-diketone products were formed
41. M. L. N. Rao, V. Venkatesh, P. Dasgupta, Tetrahedron Lett. 2010, 51, 4975.
42. H. Yamamoto, N. Momiyama, Chem. Commun. 2005, 3514-3525.
43. B. T. Worrell, J. A. Malik, V. V. Fokin, Science 2013, 340, 457-460.